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PubMed2005

GH97 is a new family of glycoside hydrolases, which is related to the alpha-galactosidase superfamily.

BACKGROUND: As a rule, about 1% of genes in a given genome encode glycoside hydrolases and their homologues. On the basis of sequence similarity they have been grouped into more than ninety GH families during the last 15 years. The GH97 family has been established very recently and initially included only 18 bacterial proteins. However, the evolutionary relationship of the genes encoding proteins of this family remains unclear, as well as their distribution among main groups of the living organisms. RESULTS: The extensive search of the current databases allowed us to double the number of GH97 family proteins. Five subfamilies were distinguished on the basis of pairwise sequence comparison and phylogenetic analysis. Iterative sequence analysis revealed the relationship of the GH97 family with the GH27, GH31, and GH36 families of glycosidases, which belong to the alpha-galactosidase superfamily, as well as a more distant relationship with some other glycosidase families (GH13 and GH20). CONCLUSION: The results of this study show an unexpected sequence similarity of GH97 family proteins with glycoside hydrolases from several other families, that have (beta/alpha)8-barrel fold of the catalytic domain and a retaining mechanism of the glycoside bond hydrolysis. These data suggest a common evolutionary origin of glycosidases representing different families and clans.

Amino Acid Sequence↗

PubMed2005

Effects of phenylethanoid glycosides from Digitalis purpurea L. on the expression of inducible nitric oxide synthase.

We have isolated four different phenylethanoid glycosides (purpureaside A, desrhamnosyl acteoside, calceolarioside B and plantainoside D) from the leaves of Digitalis purpurea (foxglove). The effects of these glycosides on activator protein-1 (AP-1)-mediated inducible nitric oxide synthase (iNOS) gene expression in the Raw264.7 macrophage cell line have been studied. Of these four glycosides, purpureaside A potently inhibited iNOS induction by lipopolysaccharide (LPS). Increase in iNOS mRNA by LPS was completely suppressed by purpureaside A. Purpureaside A did not significantly affect LPS-inducible nuclear factor-kappaB (NF-kappaB) activation or the nuclear translocation of p65. Moreover, a reporter gene assay using AP-1 specific luciferase reporter revealed that the enhanced activity of AP-1 by LPS was completely abolished in cells treated with purpureaside A. These results demonstrated that purpureaside A inhibited LPS-inducible iNOS expression in macrophages through the suppression of AP-1, but not of NF-kappaB.

Cell Line↗

PubMed1993

Pre-column derivatization and its optimum conditions for quantitative determination of urinary hydroxylysine glycosides by high-performance liquid chromatography.

A method has been developed for rapid analysis of the urinary hydroxylysine glycosides [glucosyl-galactosyl-hydroxylysine (GGH) and galactosyl-hydroxylysine (GH)] as collagen metabolites. The glycosides were fluorometrically derivatized with 5-dimethylaminonaphthalene-1-sulfonyl chloride, and then subjected to reversed-phase high-performance liquid chromatography using a gradient system. Suitable standard hydroxylysine glycosides which were not diastereoisomers were prepared from human urine. Urinary GGH and GH were analyzed within 1 h, including column washing. This method was applied to the urine samples of 68 healthy persons of different ages.

Adult↗

PubMed1996

Cytotoxic activities of solanum steroidal glycosides.

Cytotoxic activities of 20 steroidal glycosides obtained from Solanum genera plants were examined against various cell lines to provide new evidence as follows: 1) As regarding the sugar linkage, the glycosides possessing a beta-chacotriosyl moiety were the most effective and the presence of the terminal rhamnosyl residue was required for exhibiting strong activity. 2) As for the aglycone, the glycosides carrying a spirostanol aglycone showed the strongest activity and even an aglycone without a sugar linkage presented considerably strong activity.

Antineoplastic Agents↗

PubMed1993

Comparative studies on the constituents of ophiopogonis tuber and its congeners. VIII. Studies on the glycosides of the subterranean part of Ophiopogon japonicus Ker-Gawler cv. Nanus.

Two monoterpene glycosides, tentatively named OJV-I (1) and OJV-II (2), and eight steroidal glycosides, tentatively named OJV-III (3), OJV-IV (4), OJV-V (5), OJV-VI (6), OJV-VII (7), OJV-VIII (8), OJV-IX (9) and OJV-X (10), were isolated from the butanol-soluble fraction of the fresh subterranean part of Ophiopogon japonicus KER-GAWLER cv. Nanus. Among these compounds, 1, 2, 3, 4, 5, 6 and 7 were identified as l-borneo1 O-beta-D-glucopyranoside, l-borneo1 O-beta-D-apiofuranosyl (1-->6)-beta-D-glucopyranoside, ophiopogonin B, glycoside C, ophiopogonin D, Ls-10, and ruscogenin 1-O-sulfate, respectively. The structures of compounds 8, 9, and 10 were established to be (23S,24S,25S)-23,24-dihydroxyruscogenin 1-O-[ alpha-L-rhamnopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->3)]-alpha-L-arabinopyranoside 24-O-beta-D-fucopyranoside, (23S,24S,25S)-23,24-dihydroxyruscogenin I-O-[alpha-L-2,3,4-tri-O-acetylrhamnopyranosyl(1-->2)][beta-D-xylo pyranosyl(1-->3)]-alpha-L-arabinopyranoside 24-O-beta-D-fucopyranoside, and (23S,24S,25S)-23,24-dihydroxyruscogenin 1-O-[alpha-L-2,3,4-tri-O-acetylrhamnopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->3)]=alpha-L-arabinopyranoside 24-O-beta-D-fucopyranoside, respectively.

Carbohydrate Sequence↗

PubMed1994

Triterpene glycosides from thalictri herba. II.

Five new triterpene glycosides were isolated from the methanolic extract of Thalictri Herba (Takatogusa), the dried aerial parts of Thalictrum sp. plants (Ranunculaceae). They were designated as thalictosides III (1) and IV (2), being cycloartane-type glycosides, and thalictosides VI (3), VII (4) and VIII (5), being oleanene-type glycosides. By chemical and spectroscopic evidence, their structures were elucidated as 22R-21S,23R-epoxy- and 22R-21R,23R-epoxy-21-methoxycycloart-24-en-3 beta,22,30-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]- beta-D-glucopyranosides (1 and 2, respectively), 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L- rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester (3) and 3-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha- L- rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl oleanolic acid and hederagenin 28-O-beta-D-glucopyranosyl esters (4 and 5, respectively).

Carbohydrate Sequence↗

PubMed1996

Two new monoterpene glycosides from ku-ding-cha. Inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT).

Two new monoterpene glycosides, kudingosides A and B, were isolated from Ku-Ding-Cha (Ligustrum pedunculare REHD.), together with a known monoterpene glycoside, (S)-lipedoside B-III, and three known phenylethanoid glycosides. Their structures were elucidated by spectroscopic and chemical means. Kudingosides A and B, and (S)-lipedoside B-III inhibited acyl-CoA: cholesterol acyltransferase (ACAT) with IC50 values of 2.70 x 10(-3)M, 2.88 x 10(-3)M, and 2.69 x 10(-4)M, respectively.

Acyclic Monoterpenes↗

PubMed1997

Bioactive saponins and glycosides. VIII. Notoginseng (1): new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, and -D, from the dried root of Panax notoginseng (Burk.) F.H. Chen.

The glycosidic fraction from the dried roots of Panax notoginseng (Burk.) F.H. Chen was found to show protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid beta-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb1 using photosensitized oxygenation, as follows: notoginsenoside A; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta, 12 beta,20(S),25-tetrahydroxydammar -23-ene; B; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D- glucopyranosyl] 3 beta, 12 beta,20(S)-trihydroxydammar-25-en-24-one, C; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D -glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta,12 beta,20(S)- trihydroxy-24 zeta-hydroperoxydammar-25-ene, and D; 3-O-[beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-xylopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl]20(S)-protopanaxadiol, respectively.

Animals↗

PubMed1999

Acylated flavonol glycosides with anti-complement activity from Persicaria lapathifolia.

During a search for biologically active compounds from traditional medicines, a crude extract of Persicaria lapathifolia was found to have anti-complement activity. Bioassay-guided chromatographic separation of the active constituents led to the isolation of a new acylated kaempferol glycoside (1) and three known acylated quercetin glycosides (2-4). The structures of compounds 1-4 were characterized as kaempferol 3-O-beta-D-(6"-p-hydroxybenzoyl)-galactopyranoside, quercetin 3-O-beta-D-(6"-feruloyl)-galactopyranoside, quercetin 3-O-beta-D-(2"-galloyl)-rhamnopyranoside and quercetin 3-O-beta-D-(2"-galloyl)-glucopyranoside, respectively. Compounds 1-4 showed strong anti-complement activity (IC50 values of 4.3, 9.7, 3.9 and 7.6 x 10(-5) M, respectively) on the classical pathway of the complement. On the other hand, six isolated flavonol glycosides (5-10) did not show any activity on this system.

Acylation↗

PubMed2000

Three new phenylethanoid glycosides from Caryopteris incana and their antioxidative activity.

Three new phenylethanoid glycosides, incanoside C, incanoside D and incanoside E were isolated together with one known glycoside, beta-D-fructofuranosyl-alpha-D-(6-O-[E]-sinapoyl) glucopyranoside from the whole plant of Caryopteris incana (THUNB.) Miq. On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 1-O-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2)-alpha-L- rhamnopyranosyl(1-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside C), 1-O-(3-hydroxy-4-methoxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2)-alph a-L- rhamnopyranosyl(1-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside D) and 1-O-(3methoxy-4-hydroxyphenyl)ethyl-O-beta-D-glucopyranosyl(1-->2) -alpha-L- rhamnopyranosyl(l-->3)-4-O-feruloyl-beta-D-glucopyranoside (incanoside E). The three new phenylethanoid glycosides exhibited radical scavenging activities against DPPH radical and inhibitory activities against the oxidation of linoleic acid.

Antioxidants↗

PubMed2000

Four new triterpene glycosides from Thalictrum squarrosum.

Four new triterpene glycosides were isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). They were designated as squarroside I, being a cycloartane-type glycoside, and squarrosides II, III and IV, being oleanene-type glycosides. Their structures were established by using two dimensional (2D) NMR techniques.

Carbohydrate Conformation↗

PubMed2002

Five triterpene glycosides from Oxytropis myriophylla.

Four new triterpene glycosides: one cycloartane-type glycoside and three azukisapogenol glycosides were isolated together with one known oleanene bisdesmoside from the Mongolian natural medicine, Oxytropis myriophylla.

Drugs, Chinese Herbal↗

PubMed2002

New glycosides from the Japanese fern Hymenophyllum barbatum.

Thirteen glycosides and methyl (3R,5R)-5-hydroxy-(beta-D-glucopyranosyloxy)-hexanoate were newly isolated from the Japanese fern Hymenophyllum barbatum, although our previous work revealed the isolation of hemiterpene glycosides, hymenosides A-J, from the same species. The structures of the newly isolated glycosides were elucidated by extensive two-dimensional (2D) NMR and/or chemical evidence. The structures of those aglycones were divided into four types, 2-methyl-but-2-ene-1,4-diol, 2-hydroxymethyl-but-2-ene-1,4-diol, 2-methylene-butane-1,3,4-triol, and 3-hydroxy-5-hexanolide. The sugar moieties, which were acylated by phenylacetic acid derivatives, were also established by chemical and spectroscopic methods. Eight glucosides of the isolated compounds in the present investigation had a bitter or weakly pungent taste. It is clear that a phenylacetyl group attached to glucose or allose as an ester is necessary for the bitter taste.

Chromatography, Gel↗

PubMed2002

New phenylethanoid glycosides from Veronica pectinata var. glandulosa and their free radical scavenging activities.

A known phenylethanoid glycoside, ehrenoside (1), was isolated together with three new phenylethanoid glycosides, verpectoside A (2), B (3) and C (4) from the aerial parts of Veronica pectinata var. glandulosa. On the basis of spectral analysis (UV, FAB-MS, 1H-, 13C- and 2D-NMR), compounds 2-4 were determined to be 2-(3,4-dihydroxyphenyl)ethyl-O-alpha-L-arabinopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-feruloyl)-beta-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-caffeoyl)-beta-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-feruloyl)-beta-D-glucopyranoside, respectively. Isolated phenylethanoid glycosides exhibited potent radical scavenging activity against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.

Biphenyl Compounds↗

PubMed2003

New aliphatic alcohol and (Z)-4-coumaric acid glycosides from Acanthus ilicifolius.

From the aerial parts of Acanthus ilicifolius, a new aliphatic alcohol glycoside (ilicifolioside C) and two new (Z)-4-coumaric acid glycosides, (Z)-4-coumaric acid 4-O-beta-D-glucopyranoside and (Z)-4-coumaric acid 4-O-beta-D-apiofuranosyl-(1"-->2')-O-beta-D-glucopyranoside were isolated. The structural elucidations were based on the analyses of spectroscopic data. Z-Form 4-coumaric acid glycosides were first isolated from plant.

Acanthaceae↗

PubMed2003

Norlanostane and lanostane glycosides from the bulbs of Chionodoxa luciliae and their cytotoxic activity.

Ten lanostane glycosides (1-10), including two new norlanostane glycosides (2 and 7) and a new lanostane glycoside with a spirolactone ring system (9), were isolated from the fresh bulbs of Chionodoxa luciliae (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis and the results of hydrolytic cleavage to be (23S)-3beta-[(O-beta-D-apiofuranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]-17alpha,23-epoxy-28,29-dihydroxy-27-norlanost-8-en-24-one (2), (23S)-17alpha,23-epoxy-29-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]-27-norlanost-8-ene-15,24-dione (7), and (23S,25R)-17alpha,23-epoxy-29-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]lanost-8-en-23,26-olide (9), respectively. The cytotoxic activity of the isolated compounds against HSC-2 human oral squamous cell carcinoma cells are also reported.

Carbohydrate Sequence↗

PubMed2005

Novel phenolic glycoside dimer and trimer from the whole herb of Pyrola rotundifolia.

From the water-soluble constituents of the whole herb of Pyrola rotundifolia (Pyrolaceae), one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4), were isolated. The structures were elucidated by spectroscopic analysis and confirmed with chemical degradation. In vitro tests for antimicrobial activity showed pyrolaside B (2) to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus luteus.

Dimerization↗

PubMed2005

Studies on the constituents of Swertia japonica Makino II. On the structures of new glycosides.

Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alco-hol glycoside, 3-butenyl 6'-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (3), and a new lignan glycoside, 7R,7'R,8S,8'S-(+)-neo-olivil-4-O-beta-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica Makino. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

Glycosides↗